Nitration of Quinoline 1-Oxide : Mechanism of Regioselectivity

スポンサーリンク

概要

• 論文の詳細を見る

• The acidity dependence of orientation in the nitration of quinoline 1-oxide was investigated by using the trifluoromethanesulfonic acid (TFSA)-trifluoroacetic acid (TFA) system and the antimony pentafluoride (SbF_5)-TFSA system. These systems provide a wider range of acidity than that of aqueous sulfuric acid. Comparison of the behavior of quinoline 1-oxide and 1-methoxyquinolinium triflate in acidic and neutral media demonstrated that O-protonated quinoline 1-oxide is nitrated at the 5- and 8-positions, and the free (unprotonated) molecule is nitrated at the 4-position. This result is consistent with theoretical expectation. It was also discovered that nitration at the 5-position increasingly predominates over that at the 8-position as the acidity is increased.

• 公益社団法人日本薬学会の論文
• 1997-02-15

著者

• SHUDO Koichi

  Faculty of Pharmaceutical Sciences, The University of Tokyo

• 大和田 智彦

  東大 薬

• Shudo Koichi

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Shudo Koichi

  Faculty Of Pharmaceutical Science Kyushu University

• YOKOYAMA Akihiro

  Faculty of Pharmaceutical Sciences, University of Tokyo

• OHWADA Tomohiko

  Faculty of Pharmaceutical Sciences, University of Tokyo

• SAITO Shinichi

  Faculty of Pharmaceutical Sciences, University of Tokyo

• Yokoyama Akihiro

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 大和田 智彦

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Saito Shinichi

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• Ohwada Tomohiko

  Faculty Of Phamaceutical Sciences The University Of Tokyo

関連論文

• ADVANCED COMPUTATIONAL DOCKING OF TWO TELEOCIDIN CONGENERS TO CYS2 DOMAIN OF PROTEIN KINASE Cδ
• Pd2 SUPERPOSITION OF TELEOCIDINS AND PHORBOL ESTERS BY A NEW COMPUTATIONAL METHOD
• (Cis)-PREFERENCE OF N, N'-DIMETHYL-N, N'-DIPHENYLGUANIDINE AND THE GUANIDINIUM SALT. CONSTRUCTION OF WATER-SOLUBLE AROMATIC LAYERED STRUCTURE
• STERICAL PRORERTIES OF N, N'-DIMETHYLUREA MOIETY ENHANCE FORMATION OF TRIPLY HYDROGEN-BONDED COMPLEXES
• ROLE OF THE HYDROPHOBIC MOIETY OF TUMOR PROMOTERS. SYNTHESIS AND ACTIVITY OF BENZOLACTAMS WITH ALKYL SUBSTITUENTS AT VARIOUS POSITIONS
• Photoaffinity Labeling of Tumor Promoter-Binding Protein (CN-TPBP) and Preparation of Affinity Sorbent Gels
• ROLE OF THE HYDROPHOBIC MOIETY OF TUMOR PROMOTERS. SYNTHESIS AND ACTIVITY OF 9-ALKYLATED BENZOLACTAMS
• EFFECT OF LIVER S9 FROM 3,4,5,3', 4'-PENTACHLOROBIPHENYL-PRETREATED RATS ON THE MUTAGENIC ACTIVITY OF THE VARIOUS CARCINOGENS TOWARD SALMONELLA TYPHIMURIUM TA 98
• Evaluation of Differentiation-Inducing Activity of Retinoids on Human Leukemia Cell Lines HL-60 and NB4
• NOVEL AROMATIC UREA DERIVATIVES WITH DNA-BINDING ABILITY
• DEIODOTRIFLUOROMETHYLATION OF ETHYL 3,3', 5-TRIIODOTHYROACETATE. DIVERGENT DERIVATIZATION BASED ON THE COMBINATORIAL CONCEPT
• New-Type Inducers of Differentiation of HL-60 Leukemia Cells Suppress c-myc Expression(Medeicinal Chemistry,Chemical)
• Effect of Am-80, a novel retinoid derivative, on contact hypersensitivity caused by repeated applications of hapten in mice
• Nitration of Quinoline 1-Oxide : Mechanism of Regioselectivity
• 軌道非対称化によるπ反応面選択
• 新カチオン活性種の関与する芳香族求電子反応
• ORBITAL DISTORTION IN DIBENZOBICYCLO[2.2.2]OCTATRIENES. BIASED EPOXIDATION AND DIHYDROXYLATION OF THE OLEFIN MOIETY
• ジカチオンおよびトリカチオンの関与するフリーデル・クラフツ反応
• The Hammett Acidity Function H_0 of Trifluoromethanesulfonic Acid-Trifluoroacetic Acid and Related Acid Systems. A Versatile Nonaqueous Acid System
• ORBITAL DISTORTION ARISING FROM REMOTE SUBSTITUENTS NITRATION AND REDUCTION OF SPIRO[CYCLOPENTA-1,9'-FLUORENE]-2-ONES
• ベンゼンと反応する求電子活性種について
• 芳香族性で終わらせないC60の化学 (1991年の化学-5-)
• 置換エチレンジカチオン
• Structural Identification of a Major Cytokinin in Coconut Milk as 14-O-{3-O-[β-D-Galactopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-arabinofuranosyl]-4-O-(α-L-arabinofuranosyl)-β-D-galactopyranosyl}trans-zeatin Riboside
• Orbital Unsymmetrization of Olefins Arising from Non-equivalent Orbital Interactions. σ-π Coupling in Bicyclo[2.2.2]octenes
• meso-DNAs with Homopurine Sequences : Analysis of Their Interaction with Natural DNAs
• Location of Two Photoaffinity-Labeled Sites on the Ligand-Binding Domain of Retinoic Acid Receptor α
• Twist Form of Teleocidin Derivatives is Active in in Vivo Tumor Promotion by (-)-Benzolactam-V8-310
• π-Conjugation in Y-Shaped Configuration. Does a Special Stability Exist?^
• Isolation and structure determination of a mutagenic substance in L-lysine pyrolysate.
• Isolation and structure determination of mutagenic substances in L-glutamic acid pyrolysate.
• Tumor promoting activities of new synthetic analogues of teleocidin.

もっと見る 閉じる

スポンサーリンク